Bromine → 4-[5-Amino-1-(6-phenoxy-benzothiazol-2-yl)-1H-[1,2,4]triazol-3-ylamino]-benzenesulfonamide

HRID 601066Notes

Reaction equation

HRID 601066 reaction equation
BrBr.[O:3]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([N:19]2[C:23]([NH2:24])=[N:22][C:21]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([S:32](=[O:35])(=[O:34])[NH2:33])=[CH:28][CH:27]=3)=[N:20]2)=[S:18])=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>ClCCl.C(O)(=O)C>[NH2:24][C:23]1[N:19]([C:17]2[S:18][C:12]3[CH:11]=[C:10]([O:3][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=4)[CH:15]=[CH:14][C:13]=3[N:16]=2)[N:20]=[C:21]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([NH2:33])(=[O:34])=[O:35])=[CH:28][CH:27]=2)[N:22]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 589764675-Amino-3-(4-sulfamoyl-phenylamino)-[1,2,4]triazole-1-carbothioic acid (4-phenoxy-phenyl)-amide

Product 1

HCID 589764114-[5-Amino-1-(6-phenoxy-benzothiazol-2-yl)-1H-[1,2,4]triazol-3-ylamino]-benzenesulfonamideYield 7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Bromine (7 μl, 1 equivalent) was added to a stirred suspension of 5-amino-3-(4-sulfamoyl-phenylamino)-[1,2,4]triazole-1-carbothioic acid (4-phenoxy-phenyl)-amide in dichloromethane (3 ml). The reaction mixture was stirred at room temperature for 18 hours. A solution of bromine (7 μl) in acetic acid (1 ml) was then added to push the reaction to completion: the reaction mixture was stirred for a further four hours. A white solid precipitated and was removed by filtration to afford the title compound (5 mg; 7% yield). 1H NMR (400 MHz, DMSO-d6) 7.05-7.20 (8H, m), 7.35-7.50 (4H, m), 7.70-7.75 (2H, d), 7.80-7.85 (2H, d), 9.90-9.95 (1H, s); MS (ES+) m/e=480

Workup

  1. customthe reaction to completion
  2. stirringthe reaction mixture was stirred for a further four hours
  3. customA white solid precipitated
  4. customwas removed by filtration

Sources & evidence

ORD record
ord-9045ec227c094215a061a223c921cdf4
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

Loading…